If you have a extra 8k, I can think of a million other places to spend it before buying a more expensive box, which shoots all the exact same approaches as your existing 530.
All you really need to update is the nav data from Jepp
http://jeppdirect.jeppesen.com/legal/charts/ads-overview.jsp?kwpgus=&cid=sem90044776
If you're VFR, I wouldn't bother unless your data is over 2 years old.
As for WAAS, for now, depends, for me I wouldn't see too much of a diffrence in IFR where I live not having it. later with the ADSB thing, you might need it if you need a certified WAAS data source, the ADSB would also put traffic on your 530, though the complementary VNAV from WAAS on many RNAV approaches is nice.
The WAAS upgrade is like $3600, plus install, which normally is just a antenna and maybe some coax cable.
Don't worry about the terrain, mountains don't move much, and if you're looking at your screen to avoid towers, well you're doomed